Browse All Oak Park IL 5 Bedroom Properties for Sale

5 Beds ⋅ 2 Baths ⋅ 12692248 MLS ⋅ ACTIVE Status

Tucked away on a quiet cul-de-sac, this truly special Queen Anne Victorian is brimming with the character, charm, and architectural detail that make it one of a kind. Thoughtfully restored and impeccably maintained, the home offers three levels of gracious living space plus a large basement with roughed-in plumbing, ready for storage, hobbies, a workshop, or future finished living space. Step into the welcoming foyer and be greeted by original oak woodwork, a stunning wraparound staircase, a built-in bench, custom radiator covers, art glass windows, and generous, sun-filled rooms throughout the main level. The spacious living and dining rooms flow easily into an open kitchen overlooking the family room/den - perfect for everyday living and effortless entertaining. A private office, which could also function as a first-floor bedroom and half bath, adds extra flexibility. Upstairs, the second level offers four bedrooms, a full bath, and a dedicated laundry room. The finished third floor offers even more versatility, featuring a vaulted-ceiling rec room with a skylight, a lofted nook ideal for reading or cozy hangouts, and a fifth bedroom that could also serve as an office, guest space, studio, or creative retreat. Set on a wide 50-foot lot, the outdoor living is equally impressive: a classic wraparound porch, a New York bluestone patio in the landscaped backyard, and a three-car garage. The home's exceptional Victorian trim and ornate architectural detailing earned it a spot on Oak Park's 2013 Painted Lady Tour. Ideally located near the Metra, Green Line, shops, restaurants, downtown Oak Park, and I-290, this quintessential Oak Park treasure is a rare opportunity to make it your own.

425 Clinton Avenue, Oak Park

$899,000

5 Beds ⋅ 4 Baths ⋅ 12608182 MLS ⋅ CONTINGENT Status

Get ready to be wowed by this surprisingly spacious, sundrenched, mid-century stunner in the perfect, heart-of-Oak Park location! This must-see, unique, tri-level home built in 1971 offers loads of space and options for the best of modern living on a tranquil, picturesque street with grand homes. Through the side entrance, be welcomed into the foyer and appreciate the gleaming hardwood floors, tall ceilings, and large, bright windows that flood the home with light. Gather with loved ones in the vast living room, spacious enough for multiple conversation areas for entertaining, or perfect for cozy nights in. And easily host your largest holiday gatherings in the adjacent dining room with two walls of windows for year-round sunlight! Cooking your gourmet meals or everyday snacks is a delight in the bright, clean, kitchen with all new stainless steel appliances ('26), including an induction stove; miles of new countertops ('26); new floors ('26); new heating ('26); quality, spruced-up cabinetry, with plenty of space to add an eat-in table or island for extra prep space. A convenient powder room and coat closet complete this level. Head up a short flight of stairs to find three fantastic, bright bedrooms, all with great closets and an oversized hallway bath with a stylish new double vanity and updated fixtures. And we're only getting started with the space! A few stairs down from the first floor, you'll find an absolutely gigantic sunken family room with bright, tall windows and tons of space - perfect for a play area, hosting family game nights, movie nights or for watching the big game with friends. Through this room and up a few stairs at the back of the home is an incredibly spacious private primary wing! It showcases an enormous great room with large windows and a stylish full bath, with a large sitting room and bedroom. The sitting room boasts huge, south-facing windows, and leads to the bedroom, which easily fits a king-sized bed and overlooks the serene backyard - your perfect oasis wing. But wait, there's more! From the lower level sunken family room, a private side hallway leads to a bedroom with a convenient full bath, and a few more stairs down from this level is yet another massive rec room with new luxury vinyl plank ('25) that leads to a spacious laundry room/kitchenette with new laundry ('26); new kitchenette with new cabinets ('26) for even more space and options. Al-fresco, the generous space continues with a backyard boasting a lovely brick-paver patio for your warm-weather entertaining and dining and a two-car garage with adjacent additional parking for two cars. This 4,500 plus sq feet home, with three private entrances, has plenty of intergenerational living and income-generating options (and with the rear wing sitting room already plumbed, easily add a kitchenette, laundry, or even a wet bar to this wing) to effortlessly make it work for your needs - a business, in-laws, nanny, teen, guests or Airbnb - and house hack your way into being a Real Estate Mogul! So much has been done in this home in 2025-2026 - fresh paint throughout; new appliances throughout; most light fixtures updated; updated floorplan; new flooring, new heating and new plumbing in some parts of the home; and so much more. This almost-ground-level, deceptively large, move-in ready home can easily adapt as your needs evolve and is in a premium location in Oak Park with friendly neighbors - just moments from all this lovely village offers - schools, cafes, shopping, dining, library, movies, pool, parks, dog park, the farmers' market, public transportation, and so much more - all at your fingertips. This updated gem with options galore is the one you've been waiting for--welcome home!

141 Wesley Avenue, Oak Park

$465,000

5 Beds ⋅ 3 Baths ⋅ 12667016 MLS ⋅ ACTIVE Status

Nestled directly across from beautiful Maple Park, this spacious 2-flat presents a rare opportunity for homeowners, investors, and value-add buyers alike. Situated on an oversized lot, this property offers generous living space, strong rental potential, and room to create additional equity through future improvements. The building features two sizable units with classic character and functional layouts. The unfinished basement provides exciting upside with the potential to duplex the first-floor unit, creating expanded living space, a larger owner's suite, or an enhanced income-producing configuration (subject to municipal approval). Enjoy scenic park views, abundant natural light, and a location that combines neighborhood charm with convenient access to schools, shopping, dining, and transportation. Whether you're looking to live in one unit while collecting rental income, renovate and increase value, or add a strong asset to your portfolio, this property offers multiple paths to success.

1032 S Maple Avenue, Oak Park

$970,000

5 Beds ⋅ 3 Baths ⋅ 12662583 MLS ⋅ ACTIVE Status

Discover this beautifully renovated 5-bedroom, 3-bath traditional American Foursquare home located in Oak Park's nationally recognized Ridgeland/Oak Park Historic District and within the highly sought-after William Beye School District. Thoughtfully transformed for modern living, the home blends restored exterior charm with today's high-end finishes and updated systems throughout. The original exterior wood siding has been carefully restored to its historical character, preserving the home's timeless appeal. The main level features a stunning new chef's kitchen with stainless steel appliances, quartz countertops, custom cabinetry, farmhouse sink, pot filler, and designer touches. A versatile main-floor bedroom and full bath offer ideal space for guests or a home office. The second level includes three spacious bedrooms with a shared bath, along with a primary suite showcasing a wet room sanctuary bath and walk-in closet. The finished lower level provides flexible living space perfect for a playroom, gym, or additional lounge area, plus a dedicated laundry room. Enjoy true peace of mind with extensive upgrades throughout the home, including a brand-new roof and gutters, energy-efficient windows, a dual-zone HVAC system, upgraded 200-amp electrical panel with all-new wiring, completely updated plumbing with a new copper water service line, and a high-efficiency tankless water heater. Conveniently located off Lake St only a few steps from Stevenson Park, Ridgeland Green Line L, One Lake Brewing Company, gymnastics center, Ridgeland Commons Aquatic Center and Ice Rink, Oak Park & River Forest High School, Pete's Fresh Market, and minutes from Downtown Oak Park. Don't miss this rare chance to own a true turn-key home where timeless historic charm is seamlessly blended with modern luxury!

131 N Taylor Avenue, Oak Park

$495,000

5 Beds ⋅ 3 Baths ⋅ 12585413 MLS ⋅ PENDING Status

Excellent investment opportunity in the heart of Oak Park! This classic vintage brick fully occupied legal three-flat offers a true multi-unit layout featuring one spacious three-bedroom unit and two renovated 1 bedroom(s). ALL units have their own washer & dryers a huge plus for tenants. The building showcases charming vintage character while providing strong income potential for investors or owner-occupants alike. Additional income from the 2 garage spots and tandem exterior spots. Each unit offers comfortable living spaces with natural light and timeless architectural details that reflect Oak Park's historic charm. Situated on a desirable tree-lined street, the property enjoys a prime location close to public transportation, parks, shopping, dining, and everything that makes Oak Park one of Chicagoland's most sought-after communities. With its classic structure, flexible living arrangements, and outstanding location, this legitimate three-flat presents a rare opportunity to own a piece of Oak Park while generating rental income. New windows on upper level. Newer boiler and roof was resurfaced few years ago. Full basement with storage for each unit. Rare opportunity! As-Is sale. More financials and lease detail upon request. Tenants Rights. Allow 72 hours for showing requests.

511 N Taylor Avenue, Oak Park

$650,000

5 Beds ⋅ 3 Baths ⋅ 12563604 MLS ⋅ ACTIVE Status

WELCOME TO THIS GREAT SPACIOUS OVER 2900 SQFT OAK PARK 2 STORY BUNGALOW THAT OFFERS 5 BEDROOMS, 2 1/2 BATHS, WITH A LARGE EAT-IN KITCHEN AND A WALK IN PANTRY, A FULL WALK-OUT BASEMENT, INCLUDING 2 CAR GARAGE, AND A LARGE FENCED YARD. CONVENIENTLY CLOSE TO SHOPPING, DINING, SCHOOLS, AND PARK. QUICK AND EASY ACCESS TO BOTH PUBLIC TRANSPORT AND HIGHWAYS!

514 S Humphrey Avenue, Oak Park

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